From May to December
by Crittab
Summary: Jeff works through his own May/December romance in his journal.


**Title:** From May to December

**Rating:** PG

**Warnings/Spoilers:** Up to the end of season 3

**Summary:** Jeff works through his own May/December romance in his journal.

**Disclaimer:** I don't own Community, yo.

* * *

**From May to December**

* * *

**May, 2012**

Dear Journal,

We're finally back at Greendale after two dark months. I can't tell you how relieved I am to have the 'darkest timeline' finally out of the way.

Well, it seems like it's out of the way, but Troy is still gone, Abed is still slipping, Annie is... well... I don't know. Things have changed, somehow. Even before we left Greendale there had been a shift, beginning just prior to our Biology exam (the exam that never actually happened). I don't know where it came from, but she doesn't look at me the way she used to. It feels like our link, the one thing that's always assured me that Annie and I had something special, has been severed.

A year ago I would have welcomed this. A year ago I was telling Annie that our moments were all in her head and that she was immature to believe in the idea of 'us'. A whole lot has changed in a year. Me, especially. I've changed.

Our third year at Greendale, or, as Abed would put it, our third _season_ changed me. I fought harder than ever to be a part of the group, something that I never would have done in the past. I realized that I _need_ these people, which is difficult for me to admit. I admitted that I have feelings for Annie, which was terrifying, but exhilarating all at once. I let them down and I regained their trust in one fell swoop. We played, we laughed, we fought, we learned, and through it all, I changed.

And through it all, right under my nose, Annie changed too. She grew up. She figured herself out and she realized somewhere along the line that she didn't need me anymore. I don't know what I was to her – and ideal, maybe. An opportunity to prove that the tin man has a heart. Now it seems like she doesn't need that kind of person anymore.

Not that Annie doesn't still love me. She does. She treats me just like she treats everyone else – like a friend who is worth all of her attention and affection.

But she used to treat me like I was more than that. I miss that.

I don't know what happened, but this shift... the shift in the group and the shift between me and Annie...it doesn't sit well.

Jeff

* * *

**June, 2012**

Dear Journal,

I should have quit and become a used car salesman or something. I could do it. I could talk people into buying hunks of junk for a buck. I don't need to be a lawyer again. I don't need anything that requires _this. _Summer school. Whoever invented summer school, I'm sure, is enjoying one of the warmer corners of Hell for it.

It's been pointed out to me several times now, by several people, that I complain about this summer school situation a _lot_, but quite frankly, I don't care. This sucks. This _more than_ sucks. This is like being repeatedly kicked in the face.

And what the _hell_ is cellular mitosis?!

Ugh.

It might be more bearable if things were back on track with the group, but honestly, they're just sliding and sliding as each day goes by. We get to see Troy sometimes, but not nearly often enough. He occasionally sneaks away from the AC repair school for covert meetings, but he's inevitably dragged back within moments. It's absolutely insane. Maybe if I was a lawyer still I could argue his case for unlawful imprisonment, but as it stands, I don't really know what I can do to help.

And having Troy gone set up this horrible chain reaction of crazy. Abed is completely losing touch with reality. He spends most of his time dressed as Inspector Spacetime, looking for Constable Reggie. I even tried to cosplay (yes, I know the word cosplay) Reggie once, but Abed just looked at me and said he doesn't have the _space_ for this. I don't even know that that means!

And then there's Britta. I wish I could take a picture of modern-day Britta and show it to her 2009 self. She would lose her shit! Britta's become this sad little love-sick puppy, and it's equal parts hilarious and horrifying. I mean, I've often wished I could have this effect on women, but it's actually making me nervous now. Yesterday I saw her writing, "Mrs. Troy Barnes," in her textbook, without hyphenating. Something is very wrong.

And then there's Annie. Annie who has been so wrapped up in making sure Abed stays this side of sane that she hasn't even _looked_ at me for a month. If I didn't know better, I'd think she and Abed had something going on (they do live alone together now...). I don't want to think of that, though. It's embarrassing to admit, but the thought of Annie being with someone else drives me insane. I know I could probably remedy that by asking her out, but honestly, I'm not sure what she'd say now. I'm not used to being the powerless one in my relationship with Annie. It's not a position I'm comfortable in.

I never thought I'd say this, but we need Troy back.

Jeff

* * *

**July, 2012**

Dear Journal,

Oh, hey, did you know Inspector Spacetime has had fourteen Constables other than Reggie? Yeah, there was Geneva, Rosamynd, Coralyn, Aselyn, Infacto, Asure, Nova, Nubind, Zesty Doritos (product placement kept the show on the air for season 23), Lonis, Jovian, Teboula, Claus and Sistina.

How do I know this, you ask?

Well, it all started about three weeks ago, when Annie assigned all of us days of the week in which it was our responsibility to keep Abed from going off the deep end. Britta has to make sure he's occupied Monday and Thursday, Annie has Tuesdays and evenings, Shirley has Thursdays and Fridays, Pierce has Sundays and I have Saturdays.

And Saturday just happen to be 'Inspector Spacetime Day' in the Abennie (formerly Trobed) apartment. I've watch 24 seasons in three weeks. Granted, the seasons are only six episodes long, but I can't take much more of this. I've started dreaming in British.

There was a time when I would do anything for Annie... and unfortunately, that time is now. I want so badly to tell her where to shove it, but I can't. I love Abed, so I'm happy to help (even if it involves this level of torture), but more than that, I'm just trying to get back in Annie's good graces. I don't know what happened all those months ago to turn her off of me, but I'm not willing to stand by and let her slip through my fingers. I know this whole Inspector Spacetime thing is sort of a passive aggressive way of getting her to like me again, but it seems to be doing the trick.

I can watch... 18 more seasons of this...

I think.

Jeff

* * *

**August, 2012**

Dear Journal,

I'm not a religious man, but THANK. GOD.

I'm freaking out like a little girl right now.

Troy is back, light is restored, we are back to the prime timeline (seriously, I have spent a _lot_ of time with Abed this summer), and most of all, SUMMER SCHOOL IS OVER!

I now have... three whole weeks before the new semester starts. But you know what? Not even my abbreviated vacation could dampen my mood right now. Things are finally back to normal, in every department. Whatever was bugging Annie seems to have disappeared because she smiled at me in _that way_ the other day for the first time in _months_.

I don't know what it is about that woman that turns me into a flailing little girl, but she just does that to me. She's got me so tightly wound around her finger, and for some reason, I don't really feel the need to do anything about it. I'm happy. I'm satisfied. The world has righted itself and Annie's into me again and life is good.

Life is good.

God, I haven't felt this way in... I don't know, four years, maybe? Maybe even longer than that. Things have changed so much since my days of being a lawyer and cheating and lying. I don't find that particularly fulfilling anymore (I know, it's as big a shock to me as it is to you). Honestly, when I wake up in the morning, my first thoughts are of those six weirdos that I call friends. Before I brush my teeth in the morning, I'm checking my text messages for them, and even occasionally sending one or two out. Things have changed big-time for Jeff Winger. My former self would be so ashamed.

But I'm not ashamed. I'm okay.

For the first time in a long time, I'm okay.

Jeff

* * *

**September, 2012**

Dear Journal,

Okay. This is it. This is the first day of the end of Greendale.

I feel good about that. _Really _good, actually.

I thought that I might feel panicky about it, like the end of this year will force me away from my home and my friends, but after the past few months, I'm not scared of that anymore. I know we'll be okay, even when we don't have Greendale to keep us together anymore. We spend all of our free time together as it is, and I can't imagine that will change after the majority of us have graduated.

God, graduation sounds good right about now.

I mean, yes, I still have ten classes to get through before I can graduate and go back to being a lawyer, but those classes don't seem as scary as they did this time four years ago. They're achievable, especially with the group backing me up. With Annie backing me up.

I've made a decision in that department, by the way – one I should probably let you in on.

Graduating without giving it a shot with Annie isn't something I'm willing to do anymore. She and I have been circling each other for four years now, and I'm not going to continue that trend. I'm going to bite the bullet, man up and tell her how I feel. I think we're in a place now where doing that wont ruin everything. I hope we are, at least.

Ever since Troy's been back, things have gone back to normal. Abed is back from the brink, Britta's back to hyphenating when she writes, "Mrs. Britta Perry-Barnes," Shirley and Pierce are getting along and running their sandwich shop, and Annie's eyes light up with I enter the room again. Things are exactly the way they should be, finally.

I can't waste time though. I can't let myself miss this one golden moment of calm to make a move on Annie. I have to do it.

I still feel really nervous about it though.

It's strange. I never used to be nervous about asking women out. It was kind of a daily activity for me, actually. Ask her out, wine and dine her, sleep with her and then send her on her way. Lather, rinse, repeat.

But with Annie the stakes are higher. I'm not asking her out to get in her pants (although it would be a welcome bonus). I'm asking her out because I know what it feels like to be on the outs with her, and that's not something I ever want to experience again. That woman just has a hold on me that I've never experienced before, and I _need_ it to work out.

I've never been this invested before. That's mostly what's freaking me out, I think. It matters a lot to me that it all goes smoothly. If it doesn't, it's going to be really hard for me to rebound.

I think Annie would be fine either way. I don't know what happened to her over the past few years... I guess she grew up. Whatever it was, it's changed her into the most incredible, self-possessed woman I think I've ever met. She's formidable, and beautiful, and determined, and it's been kind of amazing to watch her transition.

I hope she's noted my transition too. It would make things easier for me moving forward if I had some confirmation that she believes I'm ready for all of this.

Jeff

* * *

**October, 2012**

Dear Journal,

Okay, I know I said I was going to ask Annie out last month but... well... here's the thing.

Annie started the first day of school on a mission. A mission to find herself a grad school.

When I walked into the study room on the first day of classes, half of the table was covered with college info packs, ranging from New York, to Seattle, to DC, to Chicago, to Beijing (I'm not kidding). In fact, it seemed like there was only one place that _wasn't_ represented in her search. Colorado.

I asked her about it, and she said it was time for her to, and I quote, "Spread her wings and find her place in the world."

Part of me wanted to tell her, "Your place is here, with me," but she was just so excited, so full of energy and enthusiasm... I couldn't do it. I can't trap her here with me. I can't cage her when she's ready to experience the world and all it has to offer. It would be cruel and unfair.

But god, it hurts.

Every time I see her I want to grab her and kiss her, and then I remember that she's trying to get as far away from Greendale as possible, and I step back. I can't stand in the way of her plans. I just can't.

And so I won't.

My big plan for this year was to be with Annie and graduate out of this crazy place. Annie's big plan is to find and plan her first big adventure. Her big plan is a lot better than mine.

So, like the masochist I've somehow become over the past four years, I started helping her research. I mean, at least I get to spend time with her – as much time as I can before she disappears into the great unknown.

We've spent every Thursday night looking through course descriptions and student catalogues, trying to figure out which school and which location has the most to offer. Does she want the student experience or the academic excellence? Does she want the big city or the small town? Does she want culture, arts and drama, or laid back? Is she a Harvard girl or should she really be leaning toward Stanford?

The weird thing about all of this craziness with Annie, however, is that it's opened my eyes to something. My plan these four years has been to go back to practising law the way I did it for years. I'm one of the best DUI lawyers in the state, but do I really want to do that for the rest of my life? I mean, I don't mind being a defender. I'm good at it, and I like it... but are those the kinds of people I want to defend?

Maybe this isn't the right kind of law for me. Maybe I should become a public defender, or even switch teams and become a prosecutor, representing victims and bringing them justice. Maybe I could use my powers for good instead of evil.

I don't know where I'll be at the end of this year. For the first time in years, I'm not sure where my path will lead. If there's one good thing about Annie's search for a way out of Greendale, it's that it's opened my eyes to the opportunities for my own life.

And hey, if my opportunities happen to intersect with hers, who am I to argue with fate?

Jeff

* * *

**November, 2012**

Dear Journal,

Annie has applied to schools in DC, Seattle and Toronto.

I've applied to law firms in DC, Seattle and Toronto.

I haven't told Annie yet.

It's weird, the way this search has gone for me. I started looking into what kind of specialized services all of these different firms are offering, and it opened my eyes to a lot of really unique opportunities. There's a firm in Seattle that focuses primarily on prosecuting sexual assault cases. There's a firm in DC that specializes in monitoring and managing the foster care system. There's a government funded firm in Toronto that dedicates itself to researching and prosecuting cold cases.

I had no idea these kinds of places existed. I thought: if you're a lawyer, you're a lawyer. You can specialize in DUI's or murder or divorce, but to find that whole firms have found and dedicated themselves to these causes... it's just opened my eyes to so many possibilities. Who do I want to be, when all is said and done? What kind of life to I want to lead? Do I want to spend the next thirty years putting the Ian Duncan's of the world back on the road, or do I want to get justice for children who have been molested?

I always thought that having a silver tongue meant using it to get your way, even if your way was kind of sleazy. Now I realize that having a silver tongue means I can do _anything_ with it. Use it for good, use it for bad, it's all the same muscle, I'm just using it differently.

I have a feeling Annie would be proud of these realizations she's helped me come to. I hope she is. I certainly want her to be.

I'm not picky about which of those firms I go to work for. I would be happy to do any of those things for a few years. My decision right now is based on which grad school Annie goes to. I hope she appreciates that.

God, do I hope she appreciates that.

Jeff

* * *

**December, 2012**

Dear Journal,

I told Annie that I'm going where she's going. She gave me this sly little grin and said, "I know."

I asked her how she knew, and she said she saw the online applications in my bookmarks when she was searching for schools on my laptop.

She's a crafty jackrabbit.

But it worked out anyway. Now we're on the same page.

It feels so freaking good to be on the same page, finally.

Annie kissed me. I should have kissed her first, in retrospect, but it was just such a flurry of activity. The words, "Annie, I want to be with you," had only barely left my lips before she was attacking them. It was kind of amazing.

Look, journal. I'm not a girl. I'm not going to give you all of the intimate details about what happened between me and Annie from that point forward... suffice it to say, it was _spectacular_. We're together now, finally. It's taken nearly four years of friendship to get us to this point, but we're finally here, and I couldn't be happier.

It was almost a year ago when Annie suggested I start writing in a journal, to sort out the truth for myself. Looking back on it, I don't know that I've ever received a better piece of advice. In this span of time from May to December, I've sorted more things out than I was able to manage in three years without a notebook to write in. It's incredible what you can accomplish when you shut out the voices around you and just get down to business.

Annie and I are going away at the end of this year. We're going to explore our options together. That's something I never thought would be part of my journey. It's amazing, really, what this girl has done to me. As much as she's grown up, I almost feel like I've grown up more. My world was turned upside down, and then it was righted by the most insane people I've ever met.

I know I said a few months ago that things were good again, but it bears repeating. Things are good, Journal. Things are really, really good.

Jeff

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**End**

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_Okay, so between watching all five seasons of _Chuck_ and planning my sister's wedding, I haven't done any writing in the last month, which sucks. And honestly, I'm a little fuzzy right now (her Bachelorette was last night...), so hopefully this is coherent. _

_Hope you liked it. Let me know!_


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